


First Three Times

by fuckingcommissions



Series: Ash Ketchum's Harem [3]
Category: Pocket Monsters | Pokemon - All Media Types
Genre: Anal Sex, Blow Jobs, Breast Fucking, Cunnilingus, F/M, Omorashi, Strip Tease, Vaginal Sex, commission
Language: English
Status: Completed
Published: 2017-05-26
Updated: 2017-05-26
Packaged: 2018-11-05 07:05:21
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,653
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11008410
Author URL: https://archiveofourown.org/users/fuckingcommissions/pseuds/fuckingcommissions
Summary: Three of Ash's firsts.





	1. Misty

Ash and his companions were camping one evening, and Misty woke Ash up, bringing him along with her. The two of them are barefoot, and she’s in a nightgown while he is just in his boxers and a t-shirt. She leads him upstream from their campsite, to a pond she found earlier that day that is just deep enough to swim in. Between the small waterfall leading into it and the way the moonlight shines on the area, it’s a very romantic setting for the two of them.

Ash is about to comment on this when he notices her removing her nightgown, and he falls silent as she does this. Underneath it, she reveals that she has been wearing a red bikini. Though it’s more modest than other bathing suits of its type, it is still snug, fitting her very well, and he can’t help but stare at her. As he gapes, she walks toward the water.

“I may not be as beautiful as my sisters,” she admits, “but I’m still just as good in the water as they are.” And with that, she dives in, showing Ash that she means exactly what she says as she begins to give him a special performance of the water ballet her sisters are famous for.

Ash can only watch as she puts on a breathtaking performance in the water, and she keeps him captivated for the whole of it. When it’s all over, she stands in the water and calls out to him, asking, “Did you like that?”

Rather than responding, Ash discards his t-shirt and wades into the water after her. It isn’t until he approaches her and pulls her into a hug that he says, “That was wonderful, You’re a beautiful mermaid, and your sisters are like ugly sea monsters in comparison, you know?”

Misty blushes at his words, both surprised to hear anyone talk about her like that and surprised to hear someone like Ash say something so sweet. “I’m used to being called the tomboy mermaid,” she confesses. “Not the beautiful one. Thank you.” At that, she dives below the surface of the water.

While he was hugging her, she felt how aroused he had become, and now she pulls his erection free from his boxers and takes him in her mouth, determined to get him off before she runs out of breath. Ash lets out a soft groan, relaxing immediately as she begins to blow him.

She doesn’t come up until she’s done, and she rolls her tongue over his cock, finding just wear to tease him to bring him closer, and even though it takes longer than he would expect her to be able to hold her breath, it isn’t all that long before she brings him to orgasm underwater. Even then, she doesn’t resurface immediately, and instead takes the time to swallow every bit of his seed as it spills in her mouth and down her throat, and only then does she finally return to the surface of the water.

“Wow, you held your breath for so long!” Ash says, impressed. Already, he seems to have bounced back from his orgasm, and Misty would laugh at the drastic shift in mood if she weren’t still trying to catch up on the breath she missed out on during that time. Besides, she wants to bring the mood back anyway, and enjoy the rest of their time out here alone, since it isn’t often that she gets Ash alone like this.

“Are you actually a mermaid?” he asks her, but she just shrugs before going into a backstroke,and floating around him lazily.

“Would you like to fuck your little mermaid?” is the first thing she says once she’s caught her breath. She starts floating a bit further, and he follows along eagerly, that being enough of an answer to her question. They end up in an area where the water is only waist deep, and when they’re standing there, Ash pulls her bikini bottoms to the side.

She wraps her legs around him as he pushes himself inside of her, and a few ripples extend around them in the water as he begins to fuck her. Soon enough, however, he’s thrusting into her with such force that there are splashes and waves around them rather than merely ripples, and Misty tips her head back, moaning softly in the otherwise silent night.

“Your moans sound as beautiful as a siren’s song,” Ash murmurs to her, and once again, she might have laughed if she weren’t otherwise so breathless- and, admittedly, a little bit flattered as well. It’s nice to hear him saying these kinds of things about her at long last, things she wouldn’t have even dared to fantasize about hearing from him in the past, before she finally won him over.

He fucks her harder and harder in the water, pushing her closer all while bringing himself there with her, and the sounds of their splashing and her moans and his all mingle together, and she thinks they’re lucky that they’re so secluded, because anyone would be able to tell what was going on based on sound alone. She clings to Ash, and works her hips in unison with his, even though she’s starting to get tired out from all her physical activity, and the two of them have no hope of lasting very long with both of them putting in that much effort.

When Misty comes, trembling with pleasure, it is all it takes to bring Ash to orgasm with her, and even as he climaxes, he doesn’t let go of her, supporting her in the water as they both moan in unison. For a moment, they just relax in their pleasure, but soon enough, Ash begins drifting, finding somewhere that he can sit along the pond without Misty being pulled underwater, and does all of this without pulling out of her.

It’s so warm and peaceful and she feels so secure in his arms that she can’t fight her drowsiness, and doesn’t really want to. As Ash pats her back, Misty falls asleep in his arms.

When they wake together the next morning, they shower under the waterfall to make sure that they’re somewhat clean. Of course, Ash finds himself unable to resist Misty like that, and ends up fucking her against the stone wall behind the waterfall, finishing them both off quickly enough that they’re able to get back to camp just as the other girls begin to stir.

  
  
  


 


	2. May

Ash waits by himself in a bed in a single Pokecenter room, completely naked. It’s a special night for him and May, their first night alone together, and he’s waiting for her because she said she had a surprise for him. He has no idea what that surprise may be, but he patiently waits for her anyway, excited.

Soon enough, she enters the room, dressed in something that’s never seen her in before. It’s a frilly pink dress with matching accessories, but with a skirt so short that he gets a very good look at her legs and the pink thigh high stockings she’s wearing.

“What do you think?” she asks playfully, twirling for him.

“I love it,” he replies honestly, too floored by how amazing she looks to even try to be snarky.

“Too bad I’m just dying to get it off,” she replies, and she slowly lifts one leg to kick off the heel she’s wearing, and then repeats the process with her other leg, leaving her feet bare save for the stockings. She strolls around, bending to pick them up and move them somewhere else, and as she does, she makes sure that her pose gives Ash a teasing view.

Straightening back up, she leans forward as she slowly peels off her elbow-length glove, taking her time with it like some sort of old-fashioned burlesque performer. Swaying her shoulders as she goes, she tosses the glove to the side once it’s off, and goes even slower with the other one. Even though there isn’t any music, she keeps a perfect rhythm and Ash can’t help but be impressed. May is a performer through and through.

Once her gloves are off, she makes quicker work of her remaining accessories until it’s time to remove the outer layers of her outfit. She unbuttons her blouse and shrugs it off her shoulders before swaying her hips while she brings her skirt down to the floor, kicking it away. This leaves her in only a lacy pink bra and thin pink panties, and the stockings, which she still hasn’t removed.

May bends forward and low, letting Ash get a good look at her cleavage before she unsnaps her bra from behind and lets it fall to the floor. Then, she spends around and bends the other way, pulling her panties down while wiggling her hips for him. In the end, she is left in just her stockings. She crawls on the bed and thrusts her behind close to his face, giving him a very good view of her moist girlhood while she leans over his erection.

She nestles it between her breasts, moving her arms so that it’s comfortably squeezed between them, and she shifts forward and back, allowing it to rise and fall, creating friction. While she does this, she dips her mouth down to lick and suck at the tip whenever it extends enough past her cleavage for her lips to reach. Ash lets out several soft moans in appreciation while she does this.

Wiggling her hips, she says, “You don’t have to just stare at me, you know. You can touch me, or maybe lick me down there…”

Leaning in, he wastes no time in burying his tongue in her folds and she lets out a happy moan before saying, “If you try to trace different shapes, it gets better and doesn’t get repetitive.” She resumes sucking and licking at him, but occasionally pauses so that she can give him more tips, teaching him how to properly eat a girl out. Eventually, he seems to really get the hang of it.

After a moment, he says, “I...I think I’m gonna come!” to which she replies, “I’m pretty close too.” That’s the last thing she says before bringing his cock as deep into her mouth as she can manage, until he comes and she swallows it while she is brought to orgasm as well, her juices thoroughly soaking his face.

“You’re a quick learner,” she says, once she’s recovered, and she removes his cock from her breasts so that she can stroke him back to an erection, getting him quickly ready for more. She scoots forward and brings his tip to her opening, but doesn’t push down onto him yet. Instead, she wiggles and moves her hips so that she teases his tip against her, driving him absolutely crazy in the process.

Looking back at him over her shoulder, she says, “What do you want me to do with your big, hard cock?”

“Please, ride me,” he says.

“What was that? I didn’t hear you?” He answers her again, and again she pretends not to hear him, and the two of them go back and forth until he can’t take it anymore.

“Please!” he finally shouts. “Ride me!”

“If you insist,” she replies teasingly, before doing just that. She drops onto him, letting him impale her before she begins to ride him like that, bouncing on his lap and murmuring, “Your cock feels so good in me!” and other things of that nature, repeating them as she gets closer and closer.

“Come on,” she murmurs, wiggling her hips. “You can touch me if you want!” At her words, he wastes no time in reaching to fondle at her ass, and the two of them keep up their movements until she’s brought him to a rather quick second orgasm, and she is right there with him, riding him all the way through his and hers and reveling in the feeling of him shooting off inside of her.

May happily relaxes into the afterglow, but she doesn’t have long to recover before Ash surprises her, proving that he isn’t done yet as he loops an arm under each of her legs to reach up and play with her breasts while he fucks her. And then he thrusts up into her, fucking her harder than she rode him. This time, they finish even more quickly than before due to his fast pace.

“Don’t get off me,” he says, “but turn around and face me.” It takes a bit of work, but May manages it, but when they’re face to face, Ash flips them so that he’s on top when starts fucking her for a third time. This last round is what it takes to finally satisfy him, and when he’s ready to sleep, he announces his intention of using her breasts as a pillow, and they fall asleep in each other’s arms.

~X~

When May wakes up the next morning, Ash has gone hard again inside of her despite still being asleep. She wraps her legs around him and begins bucking her hips to wake him up, but when he does wake up, it is not just because of her efforts. His bladder is rather full as well, and that helps her cause quite a bit.

“Let me up,” he mutters. “I gotta pee.”

“Oh, no! You’re not going anywhere until you give me a nice morning creampie!”

He’s not able to argue with her when she gives him a look, and he manages to hold out while he fucks her, at least long enough to bring her to orgasm and come inside of her. However, she clings to him afterwards, not letting him up in time, and he loses control, his bladder emptying inside of her.

When May realizes that that is what he’s doing, she decides that she doesn’t need to bother holding back anymore, and she lets go, warm liquid gushing onto him. This is enough to bring Ash to a second climax, and it surprises him so much that it takes him a moment to bounce back.

When he recovers, he’s able to get up while still inside of her and he carries her off to the bathroom to clean her up.

  
  
  


 


	3. Iris

Iris is doing everything she can to try to make herself look more mature for her first night alone with Ash. Wearing lacy black panties and a matching training bra- and she’s still a little bitter that she couldn’t get anything bigger to work- she rests among several pillows in a room that is only lit by the dim glow of candles. She’s posed as seductively as she can manage, and when Ash finally enters the room, she spreads her arms and her legs as a means of inviting him over.

He strips while he makes his way over to her, and climbs on top of her. Ash takes her into a passionate kiss that Iris eagerly returns, and when he breaks it, he begins trailing kisses down her neck and chest, until he’s kissing her over her bra, teasing her nipples in the process.

However, he soon looks up at her with a smirk and says, “You don’t need this for your itty bitty kiddy titties, you know?” And with that, he removes it, but before Iris can snap back at him, he rests his lips against one of her nipples, taking it between them and beginning to suck at it, causing her to give way to her passionate moans. Her nipples are incredibly sensitive, so as he teases with her, she finds herself writhing in pleasure, unable to do anything else.

When he pauses to let her catch her breath, it’s only a brief pause before he does the same to her other nipple, overwhelming her with pleasure all over again. This time, her moans are even louder than before and she becomes more and more helpless under his touch. Finally, he begins to trail kisses further down, giving her time to recover again, and she giggles when he reaches her navel and pauses to lick in it.

When Ash reaches her the waistband of her panties, he peels them off, and they’re soaked through due to her arousal. Teasingly, he says, “These are so wet...did you have a little accident or something?”

“What? No! You know that’s pussy juice!” she argues.

“I don’t know,” he says, pretending not to be convinced. “I think you might have had an accident with that little kid bladder of yours.”

“I did not!” she protests, and he laughs, before dropping the subject and moving on to other matters.

He spreads her pussy and says, “It’s a nice contrast, seeing your pretty, pink pussy against your skin tone. I wonder if you taste as good as you look.” To answer his own question, he leans his mouth down and begins to lap at her folds, recalling everything that May taught him and putting it to good use.

In fact, he puts it to such good use that it isn’t long before Iris is moaning out, “I’m gonna...I’m gonna come, Ash!” though the nipple play certainly helped get her to this point as well. When she does come, she tightens up so much that it traps Ash’s tongue within her for the moment, and also causes the contents of her half-full bladder to come gushing out.

Ash drinks all of this during the time she takes to recover from her orgasm, and then says, “See what I mean? You totally have the bladder of a little kid!”

“That’s not true!” she protests. “I did that on purpose! And, besides, I can hold a lot more than that if I’m really trying.” Though the first part is a lie, the second part isn’t, and she really hadn’t even realized that she had to pee before that happened, so she knows that she couldn’t have been very full.

He pushes her knees up until they’re resting against his elbows and prods at her with his erection. “Beg me to fuck your little kid pussy.”

“Please fuck me,” she says, her tone sincere, but she doesn’t mention the second part of his request.

“You know, the others aren’t here to buy your big girl act,” he says.

“Says the little kid trying to act like a big man!” she retorts.

“The only little kid I see here is you,” he replies.

“I could say the same thing!” They go back and forth for a bit like this, until finally, she can’t take it anymore. She whispers, “Please fuck my little kid pussy…”

“What was that?” He smirks. “You’re going to have to speak up, I can’t hear you at all like that.”

“Please fuck my little kid pussy!” she shouts, blushing furiously all the while. With that, he pushes inside of her, and begins to pound into her with abandon.

At his insistence, she finds herself saying things like, “I’m such a naughty little girl!” and “I love it when you fuck my little kid pussy!” and if she lets up the act of the little girl, he slows down his movements until she starts it back up in her desperation to be fucked.

When Ash grows close, he slows and says, “Unless you want me to pull out and shower you, you better beg for me to come in your little kid pussy.”

At this point, she doesn’t even have it in her to fight and she swallows what pride she has left, shouting, “Please come in my little kid pussy and flood my little kid womb and make my little kid stomach swell and let me use my little kid pussy to milk you dry!”

When he comes, she is brought right there with him, tightening again so that he is trapped within her, and her stomach bulges out slightly as he fills her womb. He waits for her to recover enough for him to pull out, and then he commands her to get on her hands and knees, which she does. He expects her to fuck her from behind, but first, he begins rubbing his cock between her cheeks, and she moans into the pillow.

That is when Ash takes her by surprise, ramming his cock inside of her there, causing her to scream out in surprise and pain. “Wrong hole!” she chokes out, panic clear in her voice.

“Now, now,” says Ash, “Dawn was my first pussy fuck and Misty my first blow job and May my first titty fuck, so that means you get to be my first try with anal!” However he’s a bit less rough at that point, giving her a chance to adjust and helping her figure out how to relax so that it doesn’t hurt for her. And then he fucks her gently, thrusting in and out for her tight hole while reaching around to finger her pussy.

With the way he fingers her, it isn’t long before she’s brought to orgasm, trembling from his touch, and with that, he shoots inside of her. They two of them fall asleep with him holding her and spooning her, still buried inside her ass.

~X~

When Iris wakes up the next morning, her bladder is full and she demands to be let up, but Ash refuses and resumes fucking her ass and fingering her, bringing her to another orgasm this way. Naturally, her orgasm causes her to lose control and he laughs, teasing her about wetting the bed like a little kid.

“It’s your fault for holding me here, you know,” she mutters.

“ Or maybe it’s just because you’re a little kid. You know, big girls can actually hold their pee,” he says, and then he carries her to the shower while the two of them continue to bicker.

 


End file.
